Stereoselective synthesis of alpha-glycosyl phosphites and phosphoramidites via O-selective glycosylation of H-phosphonate derivatives.
A highly stereo- and chemoselective glycosylation of H-phosphonate derivatives with glycosyl iodides was discovered as a reverse reaction of the formation of a glycosyl iodide from a glycosyl phosphite and I- under mild acidic conditions. Further study on the unique reaction showed that the reaction provided various alpha-glycosyl phosphites and phosphoramidites in a highly stereoselective manner with complete O-selectivity.
Matsumura
Fumiko
F
Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Kashiwa, Chiba, Japan.
Oka
Natsuhisa
N
Wada
Takeshi
T
D006031:Glycosylation; D006859:Hydrogen / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry*; D017905:Phosphites / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D063065:Organophosphonates; D009943:Organophosphorus Compounds; D017905:Phosphites; C434331:phosphoramidite; D006859:Hydrogen; D010100:Oxygen